1-(3-deoxy-3-fluoro-b-D-glycero-hex-2-enopyranosyl-4-ulose)-N4-benzoyl cytosine

ID: ALA458362

PubChem CID: 44567487

Max Phase: Preclinical

Molecular Formula: C22H22FN3O9

Molecular Weight: 491.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccn([C@@H]2O[C@H](CO[C@H]3C=C(F)C(=O)[C@@H](CO)O3)[C@@H](O)[C@H]2O)c(=O)n1)c1ccccc1

Standard InChI:  InChI=1S/C22H22FN3O9/c23-12-8-16(34-13(9-27)17(12)28)33-10-14-18(29)19(30)21(35-14)26-7-6-15(25-22(26)32)24-20(31)11-4-2-1-3-5-11/h1-8,13-14,16,18-19,21,27,29-30H,9-10H2,(H,24,25,31,32)/t13-,14-,16-,18-,19-,21-/m1/s1

Standard InChI Key:  WXXMCBQEDFVBRD-QTNPILDNSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA458362

   N-[1-[(2R,3R,4S,5R)-5-[[(2R,6R)-4-fluoro-6-(hydroxymethyl)-5-oxo-2H-pyran-2-yl]oxymethyl]-3,4-dihydroxyoxolan-2-yl]-2-oxopyrimidin-4-yl]benzamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 491.43

Molecular Weight (Monoisotopic): 491.1340

AlogP: -0.73

#Rotatable Bonds: 7

Polar Surface Area: 169.44

Molecular Species: NEUTRAL

HBA: 11

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.40

CX Basic pKa: ┄

CX LogP: -0.45

CX LogD: -0.45

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.39

Np Likeness Score: 0.35

References

1. Manta S, Agelis G, Botić T, Cencic A, Komiotis D..  (2008)  Unsaturated fluoro-ketopyranosyl nucleosides: synthesis and biological evaluation of 3-fluoro-4-keto-beta-d-glucopyranosyl derivatives of N(4)-benzoyl cytosine and N(6)-benzoyl adenine.,  43  (2): [PMID:17548129] [10.1016/j.ejmech.2007.04.001]

Source

Source(1):

• Scientific Literature